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Synthesis of labelled bioactive compounds. III. 2‐(arylimino)‐imidazolidine labeled with 14 C, tritium and deuterium
Author(s) -
Stiasni M.,
Stähle H.
Publication year - 1978
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580140108
Subject(s) - chemistry , imidazolidine , ethylenediamine , methyl iodide , thiourea , potassium thiocyanate , tritium , aniline , medicinal chemistry , nuclear chemistry , organic chemistry , physics , nuclear physics
Five compounds of a group of 2‐(arylimino)‐imidazolidines, among them Clonidine (St 155), have been labeled with 14 in the following manner: Potassium cyanide‐[ 14 C] was converted to potassium thiocyanate‐[ 14 C] and subsequently to the N′‐phenylthiourea using benzoyl chloride and the corresponding aniline. The thiourea was saponified and reacted with methyl iodide to give the quaternary isothiourea derivative. Ring closure to the imidazolidine was achieved through condensation with ethylenediamine. ‐ Tritium labeled Clonidine was obtained by catalytic debromination of the 4‐bromoderivative with tritium gas. ‐ The starting material for deuteroclonidine was ethylene‐[ 2 H 4 ]‐diammonium dichloride.